Despite the aging of those in our prisons and the increasing numbers of older incarcerated individuals returning home, much of the research on reentry challenges focuses on the experiences of individuals under the age of 50. Using in-depth interviews with 19 formerly incarcerated individuals who were released after the age of 50, we examined their reentry experience, particularly in regards to finding employment. We found that while this population experienced barriers to finding a job that were similar to their younger counterparts (e.g., stigma, the lack of proper documentation, etc.), they also struggled to find employment due to age-related factors like deteriorating health, ageism, and digital illiteracy. The results from this study can help policymakers better prepare for and appropriately anticipate the needs of its older returning citizens, a group often left out of most reentry discussions.